Bis<1,4-dioxaspiro<4.5>decan-8-yliden>hydrazin | 64554-48-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Bis<1,4-dioxaspiro<4.5>decan-8-yliden>hydrazin
• 英文别名: 1,4-Dioxaspiro<4.5>decan-8-on azin；N-(1,4-dioxaspiro[4.5]decan-8-ylideneamino)-1,4-dioxaspiro[4.5]decan-8-imine
• CAS: 64554-48-9
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: GOZQPNHQQAFUSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Bis<1,4-dioxaspiro<4.5>decan-8-yliden>hydrazin 在 HOF* CH₃CN 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以95%的产率得到1,4-环己二酮单乙二醇缩酮
  参考文献：
  名称：

  一种新的有效脱保护嗪，和肟的方法。交换羰基中氧同位素的绝佳途径

  摘要：

  可以通过HOF·CH 3 CN在几秒钟内将HOS·CH 3 CN脱保护为相应的酮或醛，从而获得非常好的收率，从而可以保护作为嗪或其他CN衍生物的羰基。该反应还提供了一种非常有效的途径，可以用任何其他氧同位素（例如[18] O）取代大多数羰基的氧原子。

  DOI：

  10.1016/j.tetlet.2005.11.090
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 肼 作用下， 以 乙醇 为溶剂， 生成 Bis<1,4-dioxaspiro<4.5>decan-8-yliden>hydrazin
  参考文献：
  名称：

  Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives

  摘要：

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.

  DOI：

  10.1021/jo00119a014

文献信息

• Rupp, Helmut; Schwarz, Wolfgang; Musso, Hans, Chemische Berichte, 1983, vol. 116, # 7, p. 2554 - 2563
  作者：Rupp, Helmut、Schwarz, Wolfgang、Musso, Hans

  DOI：——

  日期：——
• RUPP, H.;SCHWARZ, W.;MUSSO, H., CHEM. BER., 1983, 116, N 7, 2554-2563
  作者：RUPP, H.、SCHWARZ, W.、MUSSO, H.

  DOI：——

  日期：——
• PEDERSEN L. D.; WEILER L., CAN. J. CHEM. <CJCH-AG>, 1977, 55, NO 5, 782-784
  作者：PEDERSEN L. D.、 WEILER L.

  DOI：——

  日期：——
• A new efficient deprotection of azines, hydrazones and oximes. An excellent route for exchanging oxygen isotopes in carbonyls
  作者：Mira Carmeli、Shlomo Rozen

  DOI：10.1016/j.tetlet.2005.11.090

  日期：2006.1

  Carbonyls, protected as azines or other CN derivatives can be deprotected by HOF·CH3CN in seconds to the corresponding ketone or aldehyde in very good yields. This reaction also offers a very efficient route for replacing the oxygen atom of most carbonyls with any other oxygen isotope, for example, [18]O.

  可以通过HOF·CH 3 CN在几秒钟内将HOS·CH 3 CN脱保护为相应的酮或醛，从而获得非常好的收率，从而可以保护作为嗪或其他CN衍生物的羰基。该反应还提供了一种非常有效的途径，可以用任何其他氧同位素（例如[18] O）取代大多数羰基的氧原子。
• Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives
  作者：Frans J. Hoogesteger、Remco W. A. Havenith、Jan W. Zwikker、Leonardus W. Jenneskens、Huub Kooijman、Nora Veldman、Anthony L. Spek

  DOI：10.1021/jo00119a014

  日期：1995.7

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.